반응 #339788

반응 방정식

1-Cyclobutyl-6-ethoxy-2-(4-ethylaminophenyl)-1H-indole-3-carbonitrile

Cyclopentyl chloroformate

chloroformate

→

[4-(3-cyano-1-cyclobutyl-6-ethoxy-1H-indol-2-yl)-phenyl]-ethyl-carbamic acid cyclopentyl ester

수율 87.0%

용매

pyridine

반응 조건

후처리

1. 1
   기타the reaction to completion
2. 2
   workup.STIRRINGAfter an additional 90 min of stirring
3. 3
   기타the reaction mixture is partitioned between aqueous HCl and EtOAc
4. 4
   기타The organic layer is dried
5. 5
   농축concentrated
6. 6
   기타Purification by silica gel chromatography

실험 절차

1-Cyclobutyl-6-ethoxy-2-(4-ethylaminophenyl)-1H-indole-3-carbonitrile (35 mg, 0.10 mmol), prepared as in example 1CO, step C, is dissolved in pyridine (300 μL). Cyclopentyl chloroformate (25 μL, 0.17 mmol) is added. The reaction mixture is stirred at room temperature for 2.5 h. More chloroformate (10 μL, 0.07 mmol) is added to drive the reaction to completion. After an additional 90 min of stirring, the reaction mixture is partitioned between aqueous HCl and EtOAc. The organic layer is dried and concentrated. Purification by silica gel chromatography yields [4-(3-cyano-1-cyclobutyl-6-ethoxy-1H-indol-2-yl)-phenyl]-ethyl-carbamic acid cyclopentyl ester (41 mg, 87%) as a white solid.

출처